Fluoroquinolones and use thereof to treat bacterial infections
The present invention relates to novel fluoroquinolones, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.
1. A compound of general Formula I:
and pharmaceutically acceptable salts thereof, wherein:
R 1 represents a saturated or unsaturated, substituted or unsubstituted, branched or unbranched alkyl group comprising 4 to 20 carbons atoms, when the alkyl group is substituted, the substituent is selected in the group comprising halo, hydroxyl, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,
R 2 represents a substituent selected from the group comprising hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,
R 3 , R 4 , R 5 and R 6 may be identical or different and each represents a substituent selected from hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,
R 7 represents a substituent selected from hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,
with the condition that the compounds of formula I are not:
7-(4-butylpiperazin-l-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-heptylpiperazin-l-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
7-(4-butyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-hexyl-3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-(4-hydroxybuty)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
with the condition that when R 2 is a hydrogen and R 7 is a fluorine, R 3 , R 4 , R 5 and R 6 are not a methyl group.
2. The compound according to claim 1 , wherein R 1 represents a saturated or unsaturated, substituted or unsubstituted, branched or unbranched alkyl group comprising 5 to 16 carbons atoms.
3. The compound according to claim 1 , wherein R 2 represents a substituent selected from the group comprising hydrogen, methyl, methoxy, ethoxy, chloro and fluoro.
4. The compound according to claim 1 , wherein R 3 , R 4 , R 5 and R 6 are identical and represent each a hydrogen.
5. The compound according to claim 1 , wherein R 7 representsa hydrogen, NH 2 or fluoro.
6. The compound according to claim 1 , having the general formula II corresponding to the general formula I wherein R 7 is a fluorine:
and pharmaceutically acceptable salts thereof.
7. The compound according to claim 1 , having the general formula III corresponding to compounds of general formula II wherein R 3 , R 4 , R 5 and R 6 are identical and represent a hydrogen atom:
and pharmaceutically acceptable salts thereof.
8. The compound according to claim 1 , selected from the group comprising:
1-cyclopropyl-6-fluoro-4-oxo-7-(4-pentylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-hexylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-octylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-nonylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-7-(4-decylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-4-oxo-7-(4-undecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-7-(4-dodecylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-4-oxo-7-(4-tridecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-4-oxo-7-(4-tetradecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-4-oxo-7-(4-pentadecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-hexadecylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-pentylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-hexylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-heptylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-7-(4-octylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-7-(4-nonylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-7-(4-decylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-undecylpiperazin-1- yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-7-(4-dodecylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-tridecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-tetradecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-pentadecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,
1-cyclopropyl-6-fluoro-7-(4-hexadecylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,
and pharmaceutically acceptable salts thereof.
9. A pharmaceutical composition comprising at least one compound according to claim 1 , or a pharmaceutically acceptable salt, and at least one pharmaceutically acceptable carrier, diluent, excipient and /or adjuvant.
10. The pharmaceutical composition according to claim 9 , further comprising a therapeutic agent and/or active ingredient.
11. A medicament comprising a compound according to claim 1 .
12. The medicament according to claim 11 , further comprising a therapeutic agent and/or active ingredient.